Diisopropylethylamine → HCID 69419383, compound

HRID 1375085Notes

Reaction equation

HRID 1375085 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)[CH3:2].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:42][C:43](O)=[O:44])[CH:28]=[CH:29][C:30]=1[NH:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH3:41])=[O:33].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:43](=[O:44])[CH2:42][C:27]3[CH:28]=[CH:29][C:30]([NH:31][C:32]([NH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[CH3:41])=[O:33])=[C:25]([O:24][CH3:23])[CH:26]=3)=[CH:17][CH:16]=2)[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 69419599[2-(4-Amino-phenyl)-indan-2-yl]-acetic Acid Ethyl Ester

Product 1

HCID 69419383HCID 69419383, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of [2-(4-amino-phenyl)-indan-2-yl]-acetic acid ethyl ester (0.158 g, Reference Example 10) in dimethylformamide (2 mL) was treated with a solution of [3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetic acid (0.169 g) in dimethylformamide (2 mL) which had been treated with diisopropylethylamine (1.3 mL) and a solution of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.223 g) in dimethylformamide (2 mL). After stirring at room temperature for 2 hours the reaction mixture was evaporated and the residue was partitioned between ethyl acetate (30 mL) and hydrochloric acid (30 mL, 0.5N). The organic phase was washed with hydrochloric acid (30 mL, 0.5N), then with saturated sodium hydrogen carbonate solution (30 mL), then dried over magnesium sulfate and then evaporated. The residual beige coloured solid was subjected to chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (2:1, v/v) to give the title compound (0.06 g).

Workup

  1. customwas evaporated
  2. customthe residue was partitioned between ethyl acetate (30 mL) and hydrochloric acid (30 mL, 0.5N)
  3. washThe organic phase was washed with hydrochloric acid (30 mL, 0.5N)
  4. dry with materialwith saturated sodium hydrogen carbonate solution (30 mL), then dried over magnesium sulfate
  5. customevaporated
  6. additionwas subjected to chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (2:1

Sources & evidence

ORD record
ord-b0119a1b56204874adefe6de50e8ead5
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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